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Lactam acetals

XIII. Ionization constants and spectral properties of N-methyl-2-aryliminolactams

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The UV, IR, and PMR spectra of N-methyl-2-aryliminolactams and their salts were examined. The ionization constants of the investigated amidines in aqueous alcohol depend substantially on the ring size (the basicities fall in the order 6 > 7 > 5). On the basis of the correlation dependences of the pK a values of the amidines and the Hammett σ constants it is shown that the π electrons of the benzene ring are conjugated both with the C=N bond and with the p electrons of the exocyclic nitrogen atom. The angles of rotation of the benzene ring with respect to the C=N bond were calculated.

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical Chemistry, Moscow

    V. G. Granik, A. M. Zhidkova, R. G. Glushkov, I. V. Persianova, E. M. Peresleni, A. P. Engoyan & Yu. N. Sheinker

Authors
  1. V. G. Granik
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  2. A. M. Zhidkova
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  3. R. G. Glushkov
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  4. I. V. Persianova
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  5. E. M. Peresleni
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  6. A. P. Engoyan
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  7. Yu. N. Sheinker
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Additional information

See [1] for communication XII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1220–1225, September, 1974.

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Granik, V.G., Zhidkova, A.M., Glushkov, R.G. et al. Lactam acetals. Chem Heterocycl Compd 10, 1060–1064 (1974). https://doi.org/10.1007/BF00472122

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  • DOI: https://doi.org/10.1007/BF00472122

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